Sodium Bicarbonate → (2-(2-Nitro-5-(piperidin-1-yl)phenyl)pyridin-4-yl)(3-(trifluoromethyl)phenyl)methanol

HRID 1408004ノート

反応式

HRID 1408004 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][N:23]=1)[CH:19]=[O:20])([O-:3])=[O:2].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:27]=[C:28]([Mg]Cl)[CH:29]=[CH:30][CH:31]=1.C([O-])(O)=O.[Na+]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[C:16]1[CH:17]=[C:18]([CH:19]([C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([C:25]([F:35])([F:34])[F:24])[CH:31]=2)[OH:20])[CH:21]=[CH:22][N:23]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 867059382-(2-Nitro-5-(piperidin-1-yl)phenyl)isonicotinaldehydeHCID 178506175HCID 178506175、化合物

生成物 1

HCID 86705939(2-(2-Nitro-5-(piperidin-1-yl)phenyl)pyridin-4-yl)(3-(trifluoromethyl)phenyl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a −78° solution of 110 mg of 2-(2-nitro-5-(piperidin-1-yl)phenyl)isonicotinaldehyde in 4 mL of THF was added 0.82 mL of a 1.0 M solution of 3-(trifluoromethyl)phenylmagnesium chloride in THF. After 5 min the solution was warmed to 0° C. and treated with 10 mL of a saturated aqueous solution of NaHCO3. The mixture was extracted with ethyl acetate and the organic extracts were washed with water and then with brine. The solution was dried (Na2SO4) and the solvent was evaporated. The residue was purified by silica gel chromatography eluting with 1:1 ethyl acetate/hexanes to give 123 mg of product. MS (ES, m/z) 458.2 [M+H]+.

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic extracts were washed with water
  3. dry with materialThe solution was dried (Na2SO4)
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 1:1 ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-c3f9e2df443a46c89ac9055567b04e9e
出典データセット
uspto-grants-2014_12
特許番号
US08916569B2

反応ノート

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